methyl 6-methoxy-2,2-dimethyl-2H-naphtho[1,2-b]pyran-5-carboxylate | 97400-66-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: methyl 6-methoxy-2,2-dimethyl-2H-naphtho[1,2-b]pyran-5-carboxylate
• 英文别名: methyl 6-methoxy-2,2-dimethyl-2H-benzo[h]chromene-5-carboxylate；methyl 6-methoxy-2,2-dimethyl-2H-benzo[h]chromen-5-carboxylate；mollugin 6-methyl ether；O-methyl mollugin；O-methylmollugin；Mollugin methyl ether；methyl 6-methoxy-2,2-dimethylbenzo[h]chromene-5-carboxylate
• CAS: 97400-66-3
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: PNVZCKPOXBYJKA-UHFFFAOYSA-N

物化性质

• 熔点：
  68-69 °C
• 沸点：
  455.1±45.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 6-methoxy-2,2-dimethyl-2H-naphtho[1,2-b]pyran-5-carboxylate 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以77%的产率得到大叶茜草素
  参考文献：
  名称：

  Synthesis of mollugin

  摘要：

  The total synthesis of mollugin, a major constituent of rubiaceous herbs, using a straightforward synthetic approach starting from 1,4-naphthoquinone via a sequence of reactions, including selective prenylation, epoxidation, reduction of the quinone moiety, acid-catalysed ring expansion, bromination, dehydration and methoxycarbonylation is presented. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.014
• 作为产物：
  描述：

  1,4-二羟基萘 在 18-冠醚-6 、 四丁基碘化铵 、 potassium hydride 、 丙酸 、 sodium hydroxide 、 苯硼酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 10.17h， 生成 methyl 6-methoxy-2,2-dimethyl-2H-naphtho[1,2-b]pyran-5-carboxylate
  参考文献：
  名称：

  Facile Synthesis of Mollugin by Kinetic Control and anti-HCV (Hepatitis C Virus) Activity of Its Analogues

  摘要：

  据报道，Mollugin具有多种生物活性，包括抗肿瘤、抗病毒（针对乙型肝炎病毒）、抗衰老和抗突变活性。本文介绍了一种从廉价的起始原料1,4-萘醌出发，通过动力学控制，两步高效简洁合成Mollugin的方法，并筛选了所制备的Mollugin衍生物对丙型肝炎病毒（HCV）的抑制能力。研究表明，二氢苯并色原烯结构可能作为一种新的领先化合物，成为额外的抗HCV药物。

  DOI：

  10.5012/bkcs.2014.35.11.3232

文献信息

• 몰루긴 유도체 화합물, 이의 광학이성질체, 또는 이의 약학적으로 허용 가능한 염, 및 이를 유효성분으로 포함하는 염증성 장질환의 예방 또는 치료용 약학 조성물
  申请人：KOREA PHARMA CO., LTD. 주식회사한국파마(119980043604) Corp. No ▼ 180111-0059112BRN ▼124-81-15899

  公开号：KR20170122970A

  公开（公告）日：2017-11-07

  본 발명은 몰루긴 유도체 화합물, 이의 광학이성질체, 또는 이의 약학적으로 허용 가능한 염, 및 이를 유효성분으로 포함하는 염증성 장질환의 예방 또는 치료용 약학 조성물에 관한 것이다. 본 발명의 몰루긴 유도체 화합물은 아민그룹의 도입을 통해 염(salt)화가 용이하여 기존의 난용성 물질인 몰루긴에 비해 용해도 개선효과가 현저할 뿐만 아니라, 상기 몰루긴 유도체 화합물을 처리하는 경우 TNF-α 또는 IL-6 유도성 HT-29 세포에서 단핵구 세포인 U937 세포의 부착을 억제하는 활성이 우수하여, 염증성 장질환의 예방 또는 치료용 약학 조성물로 유용하게 사용될 수 있다.

  This text appears to be in Korean. Would you like me to translate it into English for you?
• Efficient Synthesis of <i>cis-</i> and <i>trans-</i>3,4-Dihydroxy-3,4-dihydromollugin
  作者：Naga Venkata Sastry Mudiganti、Sven Claessens、Pascal Habonimana、Norbert De Kimpe

  DOI：10.1021/jo800312j

  日期：2008.5.1

  An efficient synthesis of naturally occurring compounds isolated from Pentas longiflora, cis-3,4-dihydroxy-3,4-dihydromollugin 2, and trans-3,4-dihydroxy-3,4-dihydromollugin 3 is described. The O-protected mollugins were dihydroxylated using OsO4 to achieve the corresponding cis-dihydroxy derivatives in excellent yield. The synthesis of trans-3,4-dihydroxy-3,4-dihydromollugin was achieved using Oxone

  描述了一种有效合成天然化合物的方法，该化合物是从五角茴香，顺式-3,4-二羟基-3,4-二氢mollugin 2和反式-3,4-二羟基-3,4-二氢mollugin 3中分离出来的。使用OsO 4将O-保护的软体动物二羟基化，以优异的产率获得相应的顺式-二羟基衍生物。使用Oxone以高收率实现了反式-3,4-二羟基-3,4-二氢mollugin的合成。提出了由甜菜碱与Oxone反应形成顺式-3,4-二羟基甜菜碱丙酮化物的机理。
• The first asymmetric synthesis of all four isomers of cis- and trans-3,4-dihydroxy-3,4-dihydromollugin
  作者：Naga Venkata Sastry Mudiganti、Sven Claessens、Norbert De Kimpe

  DOI：10.1016/j.tetlet.2008.09.138

  日期：2008.12

  Asymmetric synthesis of all the four stereoisomers of cis-3,4-dihydroxy-3,4-dihydromollugins 4 and 6 and trans-3,4-dihydroxy-3,4-dihydromollugins 5 and 7 was achieved. The O-methoxymethyl mollugin derivatives were dihydroxylated to (−)- and (+)-cis-3,4-dihydroxy-3,4-dihydromollugin derivatives using both AD-mix-α and AD-mix-β. Deprotection of the MOM-ethers of cis-dihydroxy compounds resulted in the

  实现了顺式-3,4-二羟基-3,4-二氢软体动物4和6以及反式-3,4-二羟基-3,4-二氢软体动物5和7的所有四个立体异构体的不对称合成。使用AD-mix-α和AD-mix-β将O-甲氧基甲基mollugin衍生物二羟基化为（-）-和（+）-顺式-3,4-二羟基-3,4-二氢mollugin衍生物。顺式-二羟基化合物的MOM醚的脱保护导致目标的立体异构体（-）-（3 R，4 R）-顺式-3,4-二羟基-3,4-二氢mollugin 4，（-）-（3 R，4 S）-反式-3,4-二羟基-3,4-二氢mollugin 5，（+）-（3 S，4 S）-顺式-3,4-二羟基-3,4-二氢mollugin 6和（+） -（3 S，4 R）-反式-3,4-二羟基-3,4-二氢软胶7。这些途径铺有很多困难，例如，底物与AD混合物不相容，反式-二羟基化合物的意外形成以及脱保护方案的失败。
• Facile Synthesis of Mollugin by Kinetic Control and anti-HCV (Hepatitis C Virus) Activity of Its Analogues
  作者：Da Hye Choi、Na Ri Lee、Cheol Gi Kim、Jong Woo Kim、Sang Wook Lee、Jong-Gab Jun

  DOI：10.5012/bkcs.2014.35.11.3232

  日期：2014.11.20

  Mollugin has been reported to have various biological activities including antineoplastic, antitumor, antiviral against the hepatitis B virus, anti-aging and antimutagenic activities. An effective and concise synthesis of mollugin in two steps including kinetic control from the cheap starting material 1,4-naphthoquinone has been introduced, and mollugin derivatives thus prepared are screened for their inhibition ability against the hepatitis C virus (HCV) and the dihydrobenzochromene structure might be an additional anti-HCV agent as a new leading compound.

  据报道，Mollugin具有多种生物活性，包括抗肿瘤、抗病毒（针对乙型肝炎病毒）、抗衰老和抗突变活性。本文介绍了一种从廉价的起始原料1,4-萘醌出发，通过动力学控制，两步高效简洁合成Mollugin的方法，并筛选了所制备的Mollugin衍生物对丙型肝炎病毒（HCV）的抑制能力。研究表明，二氢苯并色原烯结构可能作为一种新的领先化合物，成为额外的抗HCV药物。
• Synthesis of mollugin
  作者：Sven Claessens、Bart Kesteleyn、Tuyen Nguyen Van、Norbert De Kimpe

  DOI：10.1016/j.tet.2006.06.014

  日期：2006.8

  The total synthesis of mollugin, a major constituent of rubiaceous herbs, using a straightforward synthetic approach starting from 1,4-naphthoquinone via a sequence of reactions, including selective prenylation, epoxidation, reduction of the quinone moiety, acid-catalysed ring expansion, bromination, dehydration and methoxycarbonylation is presented. (c) 2006 Elsevier Ltd. All rights reserved.